127006 20241125101151.0 doi 10.1016/j.tet.2023.133450 sideral 133877 ART-2023-133877 eng Dorado, V. Simple metal-free oxidative cleavage of 1,2-diols 2023 Access copy available to the general public Unrestricted Cleavage of 1,2-diols is easily carried out under mild conditions with the Oxone/KBr (or Oxone/NaCl) method in either acetonitrile/water or tert-butanol/water medium at room temperature. This procedure is highly efficient for the cleavage of dihydroxyfatty esters and acids. The reaction takes place through a double oxidation of the 1,2-diol, leading to the 1,2-diketone that undergoes a Baeyer-Villiger oxidation, with a final hydrolysis of the generated anhydride. The application to other diols, including simple internal and terminal diols, is also possible, but the nature of the diol substrate conditions the optimal halide/solvent system, given that important differences in reactivity are observed. These differences are ascribed to the change in the rate limiting step depending on the substrate/halide/solvent combination info:eu-repo/grantAgreement/ES/DGA-ERDF/E37-20R info:eu-repo/grantAgreement/ES/MICINN/RTI2018-093431-B-100 info:eu-repo/grantAgreement/ES/MINECO/PID2021-125762NB-I00 info:eu-repo/semantics/openAccess by-nc-nd http://creativecommons.org/licenses/by-nc-nd/3.0/es/ 2.1 2023 CHEMISTRY, ORGANIC 24 / 58 = 0.414 2023 Q2 T2 0.406 2023 Biochemistry 2023 Q3 Organic Chemistry 2023 Q3 Drug Discovery 2023 Q3 3.9 2023 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Herrerías, C. I. Universidad de Zaragoza (orcid)0000-0002-7272-8506 Fraile, J. M. (orcid)0000-0002-0136-5138 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 139 (2023), 133450 [7 pp.] Tetrahedron TETRAHEDRON 0040-4020 605694 http://zaguan.unizar.es/record/127006/files/texto_completo.pdf Versión publicada 2762657 http://zaguan.unizar.es/record/127006/files/texto_completo.jpg?subformat=icon icon Versión publicada oai:zaguan.unizar.es:127006 articulos driver 2024-11-22-12:07:01 ARTICLE